Auranofin

CAS No:
34031-32-8 Category:
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Product Details:

  • CAS No: 34031-32-8
  • AHFC code: 00:00.0
  • Synonyms: Auroafen
  • ATC Code: M01CB03
  • Chemical Formula: C18H29NO3
  • Molecular Weight: 678.484
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00995 (APRD00808)
  • SMILES: CCP(CC)(CC)=[Au]S[C,,H]1O[C,H](COC(C)=O)[C,,H](OC(C)=O)[C,H](OC(C)=O)[C,H]1OC(C)=O
  • InChl: AUJRCFUBUPVWSZ-XTZHGVARSA-M
  • PubChem: 6333901
  • IUPAC: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-$l^{5}-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate

Additional Details

Indication:
Used in the treatment of active, progressive or destructive forms of inflammatory arthritis, such as adult rheumatoid arthritis.
Pharmacodynamics:
Auranofin is a gold salt used in treating inflammatory arthritis. Gold salts are called second-line drugs because they are often considered when the arthritis progresses in spite of antiinflammatory drugs (NSAIDs and corticosteroids).
Mode of Action:
Exactly how auranofin works is not well understood. It may act as an inhibitor of kappab kinase and thioredoxin reductase which would lead to a decreased immune response and decreased free radical production, respectively. In patients with inflammatory arthritis, such as adult and juvenile rheumatoid arthritis, gold salts can decrease the inflammation of the joint lining. This effect can prevent destruction of bone and cartilage.
Metabolism:
Toxicity:
Oral, rat: LD50 = > 2000 mg/kg. Symptoms of overdose may include diarrhoea, vomiting, abdominal cramps, and symptoms of hypersensitivity (such as skin rash, hives, itching, and difficulty breathing).
General Reference:
Jeon KI, Byun MS, Jue DM: Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKKbeta subunit. Exp Mol Med. 2003 Apr 30;35(2):61-6. Pubmed Kim IS, Jin JY, Lee IH, Park SJ: Auranofin induces apoptosis and when combined with retinoic acid enhances differentiation of acute promyelocytic leukaemia cells in vitro. Br J Pharmacol. 2004 Jun;142(4):749-55. Epub 2004 May 24. Pubmed Venardos K, Harrison G, Headrick J, Perkins A: Auranofin increases apoptosis and ischaemia-reperfusion injury in the rat isolated heart. Clin Exp Pharmacol Physiol. 2004 May-Jun;31(5-6):289-94. Pubmed Hafejee A, Winhoven S, Coulson IH: Jessnerês lymphocytic infiltrate responding to oral auranofin. J Dermatolog Treat. 2004 Sep;15(5):331-2. Pubmed Rigobello MP, Folda A, Baldoin MC, Scutari G, Bindoli A: Effect of auranofin on the mitochondrial generation of hydrogen peroxide. Role of thioredoxin reductase. Free Radic Res. 2005 Jul;39(7):687-95. Pubmed
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